Dressing with Style When It’s Cold Outside

Fall. Fall is so easy for dressing with style. I pop on an extra layer, leave my jacket open, and let my layers trap just enough heat to keep me warm. But dressing with style when it’s cold outside? For me that’s a much more difficult challenge. When it’s freezing, I only want to throw on my Patagonia jacket, lace up my duck boots, and journey out into the frozen tundra like some sort of half-assed, rejected cast member of Ski School (one of Dean Cameron’s best movies, by the way).

I find that I really have to push myself out of my comfort zone when the mercury starts dropping. The desire to stay warm outweighs the desire to look good. But I have to constantly remind myself that there are clothes that will actually let me do both. I thought I would pull together two options, one casual and one business, for a little outfit inspiration in the coming two months or so of chilly temps.

Casual Dressing with Style When It’s Cold Outside

Obviously, the first thing I reach for on cold mornings when getting dressed are my jeans. If you take a look at my Instagram at all, you will be sure to see me sporting my favorite jeans more than a few times. But I have to remind myself that there are other casual fabrics besides denim which will keep the chill at bay. Corduroy is a great option. Moleskin is too. Think of moleskin like corduroy without the ridges. I can also replace my rubber work boots with a leather pair. Cared for over the years, leather boots will age beautifully and remain as functional as a pair of rubber ones. And that nylon snow jacket? Well, I should leave that for the camping and swap in a wool car coat or peacoat. Sailors have known for generations that a wool peacoat will keep both the cold and the wetness away.

Casual Dressing with Style When It's Cold Outside
Casual Dressing with Style When It’s Cold Outside

Pants: AG Jeans  //  Shirt: Brooks Brothers  //  Sweater: J. Crew

Boots: Red Wing  //  Socks: Red Wing

Coat: Suitsupply  //  Scarf: Saks Fifth Avenue

Business Dressing with Style When It’s Cold Outside

My go to choice for business wear in the winter is a suit. I love a warm, flannel suit when it’s cold out. Whenever I wear a heavier weighted wool suit, I immediately remember why men have been wearing these for centuries. Wool flannel is such a perfect insulator; there is almost no need to mess with it. I like to layer my suit with a overcoat and scarf to create an almost impenetrable shell of wool, keeping me warm all day long. For my feet, a fresh shined pair of dress boots and wool socks are the perfect finishing touch.

Business Dressing with Style When It's Cold Outside
Business Dressing with Style When It’s Cold Outside

Suit: Brooks Brothers  //  Shirt: Charles Tyrwhitt  //  Tie: Isaia

Boots: Allen Edmonds  //  Socks: Corgi

Coat: Cardinal of Canada  //  Scarf: Eton